Shemales Porn Stories
Page 2

Jamie's Descent Part 1

Jamie's Descent

Nikkie Silk


Chapter 1

What did we do before social media? How did we manage to get through
the day without that endless stream of dirty jokes, funny photographs,
gossip and links to dodgy websites that now fill our lives? Yeah,
yeah, I can hear you grumble. Get on with it, I can hear you say. Well,
dear reader, it was one of those links that started me down the road
to... oh, you'll find out soon enough. I was 18 and I had just come
down to London from my hometown in Norfolk after leaving school.

A friend of my father's had offered me a job in an off... Continue»
Posted by nikkiesilk 10 days ago  |  Categories: First Time, Shemales  |  
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My first shemale experience

so i've read plenty of stories on this website and thought I would share my own with you from 2011

For years I had fantasised about being with a ladyboy, but didn't know how to go about it as I didn't want to pay for an e****t.
I found a ladyboy dating website and created an account, it cost $30 for the month but was still cheaper than paying for an e****t and slightly more classy.
After about a week of sending messages to compatible matches, I finally got a response from an Asian TS who was visiting from Malaysia. She said she liked my photos and wanted to meet with me that weekend, so w... Continue»
Posted by mick_c1990 10 days ago  |  Categories: Anal, First Time, Shemales  |  
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Cockatoo Part 11

Cockatoo Part 11
Nikkie Silk

Areeya returned to the apartment sometime after we had gone to bed as the moorings needed more attention than Areeya had initially thought. After she and Shane had eventually got Cockatoo 3 safely secured on the pier, he had gone back to his hotel and Areeya headed back to get some sl**p in the apartment.
In the morning I had changed back into being James, albeit with a little reluctance. Alex had suggested I go on the boat as James and change into Scarlett for the evening. I thought it was one of Alex's better ideas as I didn't have anything suitable for the... Continue»
Posted by nikkiesilk 10 days ago  |  Categories: Shemales  |  
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Be-cumming a School Girl

Be-cumming a schoolgirl
From the time I was 5 or 6 I would sneak into the lodger’s bedroom after she had left for work. I would dress up in her lingerie and climb into her warm bed. It just felt so good wearing silky clothes which felt so delicate against my skin. I just loved to feel feminine. If anyone looked in I would pull the covers up to my neck to hide what I was wearing. A few years later I would be wearing my elder s****r’s panties and occasionally my mother’s when she was out. I guess she was suspicious because one day my s****r caught me out and paraded me in front of my parents ... Continue»
Posted by Sally5050 10 days ago  |  Categories: Shemales, Taboo  |  
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Room 209: First Sex as a Crossdresser

crossdresser – trans – interracial – lgbt – first time – virgin – black cock – crossdressing – natural tits – bra

I've been crossdressing for much of my life, as far back as I can remember. I would even go to sl**p as a k** and pray that I would wake up in a girl's body. In the last few years, now that I live by myself, I spent about $1,000 on a whole wardrobe of women's clothes for myself - bras, thongs, dresses, tops, stockings, lingerie, make-up, perfume, etc... I have also been overweight for some time so I have breasts. As a man, I have to minimize them all the time. As a women,... Continue»
Posted by naughty_bi_interest 11 days ago  |  Categories: First Time, Fetish, Shemales  |  
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Mayberry, the Black Goddess

tranny – shemale - cocksucking – anal – spanking – domination – submissive

Another lonely night led me to walking down the dimly lit street and wandering into the sex shop. There wasn't too much adventure to be seen there, very comparable to my apartment.

I was looking at toys. Specifically, butt-plugs. Not that I didn't already have one; in fact, I was wearing one at the time. The little bell above the door rang.

I looked at the cashier, she stood there- blowing her bubble gum. I couldn't see who just came in. I was curious. I continued to look at the toys. I squatted to get o... Continue»
Posted by naughty_bi_interest 11 days ago  |  Categories: Anal, Fetish, Shemales  |  
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abused shemale toy strikes back

These are excerpts from a horny chat i had with a guy. All I did now was taking out our sidetalk and try to correct any errors, since we are both non native english speakers. he knows it is used here and I am sure the story will continue. I'd love some feedback to see if i will upload the next parts.
The story includes rough sex, dominance, breath play, v******e, and generally hardcore stuff, so if you are offended by that, stop reading. Since they are from a chat, perspective will change between us two, so everything from his perspective will be bold.

I come home to you. You are stan... Continue»
Posted by hikahuk 11 days ago  |  Categories: BDSM, Fetish, Shemales  |  
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Daniel Effeminate College Student Chapter 2

Chapter 2
The Party
At the end of their successful meeting Serge invited Adrian and of course Daniel to a party at the home of his employer for that evening. It was an event with a large number of people invited from the arts and business community artists, buyers and supporters of the arts and some musicians and a few from the theatre community. Adrian and Daniel arrived together and Daniel looked spectacular with his new hair style and wearing one of the new outfits which were purchased that afternoon. He felt wonderful and as he entered the large foyer. He looked in a huge mirror and admi... Continue»
Posted by colourfast 11 days ago  |  Categories: Gay Male, Mature, Shemales  |  
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Daniel Effeminate College Student

Chapter 1
The Beginning

Daniel, an Italian boy in his late teens is starting a fine arts program at a college in the US. He had been awarded a full scholarship as part of an exchange program with the international arts community. He arrives before classes begin and has to stay in a hotel at his expense as the residence on campus in not available for a week. He is happy to be there as this is freedom for the boy as he can now begin to express his true desires to be gay and effeminate. At home it was not possible with the closeness of his f****y, friends and values of his community. However ... Continue»
Posted by colourfast 11 days ago  |  Categories: Gay Male, Mature, Shemales  |  
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The Apartment Part 2

I had found myself a new flat but was just discovering that it came with strings attached. I am not sure, but they are into swapping partners at a party. I was at my first.

I was sucking George's little fat cock while his tranny wife fucked me from behind. While we are in full flow, the other couple come into the party. Roger and Diana. Diana was a plump thing with a sweet cock while Roger was tall and thin. His skin was very white and covered with dark hair. His cock was hard and he stood in front of me while Diana kissed me! She moved from me to George holding her cock out for him to suck... Continue»
Posted by dasilva1672 11 days ago  |  Categories: Fetish, Shemales  |  
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Friendship Bands

Chapter 1: At the Market

John and Craig were old friends, right back to when they were both k**s
causing trouble around the streets of South London. As they grew into
men they'd both had a keen eye for the girls and had no shortage of
success. They made a good team.

John was a natural leader with his broad shoulders, 6ft 2in height, dark
hair and handsome features. The girls would all swoon over him. Craig
was usually happy to provide back-up, chatting up the best friend of
John's preferred girl for the night and saying what a great guy John was.
"John's got hidden depths," he... Continue»
Posted by lana100 12 days ago  |  Categories: Shemales  |  
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crossdressing at techno party been fucked by 3 men

Some years ago i whent to a gigant techno party
I dicide to go and dress as a bitch
Well i was there dancing in the trance floor i was so happy to get to this place and dress sluty .
I was dancing at the back of the dancefloor sudently 3 men where getting closer to me and we finally dance togthere and having fun.
One of the guy whent to get drinks for all of as , so we drink all toghtere that was my mistake !
The guy have droped some d**gs in my glass after 30 minutes i started to feel strange . I left those guys to go to the toilet
But one of the guy followed me to the toilette when... Continue»
Posted by sissyslave78 12 days ago  |  Categories: Anal, Hardcore, Shemales  |  
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Crossdresser getting TRAINed

I was home alone when i got a call from a friend that is train driver / railroad engineer. He is 40 years old and spend most time alone driving a train. He asked me if i could not come over, because he is feeling alone. I had nothing better so i visited his flat. So i put makeup wig and some tight dress with thong and heels. I wanted to put stockings but already had heels so i decided just to go with my smooth legs, it was hot that day anyway.

He already had prepared some beer and drinks. We talked about his boring job while watching television. After a while he started rubbing his p... Continue»
Posted by Nirien 12 days ago  |  Categories: Anal, Gay Male, Shemales  |  
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Мой первый мужчина

Привет. Я расскажу реальную историю о том как я стала женщиной. Сейчас мне уже почти сорок лет, но события того лета до сих пор свежи в моей памяти.

Мне было 18 лет и я был высоким и стройным юношей. Но широкие бёдра и узкая грудная клетка отличали меня от моих атлетически сложенных ровесников. Я был романтичным и нежным и в отличии от них не интересовался футболом и мотоциклами. Я любил читать и смотреть мелодрамы и любовные истории, а на красивых и сильных мужчин смотрел с замиранием сердца. Так как я с детства считала себя девочкой, то повествование буду вести именно так.

Один такой м... Continue»
Posted by miss_slonik 12 days ago  |  Categories: Anal, First Time, Shemales  |  
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"The Leatheress", Episode 103: "Clo

As far as I was concerned, that late autumn a few years ago, I was easily the luckiest closeted crossdressing and bisexual fetishist in the world. Ever since I was quite young, I'd had a secret desire for dressing up in sexy women's clothing, painting my lips up, and smoking long cigarettes while acting out intricate fantasies about spending passionate evenings with plenty or me; real, famous, or completely imagined. But when my first opportunity to step in and indulge in these passions for real first presented itself, it happened in an amazing way. When I started a new job fresh out of colle... Continue»
Posted by SexyLeatheress 15 days ago  |  Categories: Anal, Fetish, Shemales  |  
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The Apartment!!

I had been given notice to quit my flat and was having trouble finding one to suit. Rents were way to high and the flats were to small. In desperation I appealed on facebook if anyone knew of a flat for rent that was not to expensive. I was amazed to receive a reply from a friend of a friend! I knew him a little but had never had much to do with him. He was leaving his flat and needed to find someone to take it over. He told me that he thought it would suit me. As it was just a message I was not able to ask him what he meant. I applied to the address that he gave me and got an e-mail that eve... Continue»
Posted by dasilva1672 15 days ago  |  Categories: Anal, Group Sex, Shemales  |  
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Feminized by a Black Thug



I had been with my girlfriend since college. Somehow despite being a buxom blond she didn't mind my less than average size member or my slight slim stature, we're almost the same size. We were taking a big step now that we'd graduated, we decided to move in together. My girlfriend, Katy's parents gave her their condo in the north side of Chicago. The place was incredible. 2 bedrooms, a view of the lake, and a balcony, and a sophisticated security system complete with cameras.

I hadn't found a job yet, so I was home all day while Katy was at work. This gave me time to indulge in my secre... Continue»
Posted by naughty_bi_interest 15 days ago  |  Categories: First Time, Fetish, Shemales  |  
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Sara becomes The Bride


crossdresser – transsexual – sissy – bride – slut – wedding night – lingerie – oral – stockings – anal

Becoming Sara has been the most amazing experience I have ever had in my life. Between the clothes and living as her all the time, to becoming the thing men fantasize, it has been an amazing transition.

While I had some good friends, girls like myself that I met at one of the trans bars in town, I did lack male friends. I was never a sociable person, very much an introvert but since I have dressed, that has allowed me to get out of my shell.

T was a guy that hung out at one ... Continue»
Posted by naughty_bi_interest 15 days ago  |  Categories: Anal, Fetish, Shemales  |  
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My First Time as Sara... Pt. 05

crossdresser – sissy – lingerie – anal – trap – oral – transexual – stockings – coquette – sissy boi

I've become Sara now for just about a year. One year of exploring deeply who I was, my past, my history and who I've become at this moment.

I was no longer just John, the meek man who was dumped by his fiancé for not being man enough. That skin was shed. Instead I became Sara. I became empowered and in charge of my life. It was as if panties and heels, cute girl next door dresses and sultry and sexy lingerie gave me a sense of empowerment.

I also had Steve with me the entire way. He be... Continue»
Posted by naughty_bi_interest 16 days ago  |  Categories: Anal, Fetish, Shemales  |  
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Julia Teil 01

Teil 01: In die Falle gegangen

Alles begann damals als spätpubertierender 18 Jähriger.

Die Mädels in meinem Alter interessierten sich nicht für gleichaltrige sondern für die 20-22 Jährigen und die jüngeren hatten mit Jungs noch nichts am Hut.

Da wir aber als einer der wenigen Haushalte schon DSL hatten beflügelte das Internet meine Phantasien immer mehr und der innere Druck Sex mit einem Mädchen zu haben stieg. Eines Tages erzählte mir dann mein bester Freund er hätte eine Kontaktseite im Internet gefunden und sich am Wochenende mit ner geilen 38 Jährigen getroffen.

Wie er mir so d... Continue»
Posted by ringmyding 16 days ago  |  Categories: Fetish, Gay Male, Shemales  |  
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